CA1157858A - Derives de quinazoline - Google Patents

Derives de quinazoline

Info

Publication number: CA1157858A
Authority: CA; Canada
Prior art keywords: quinazoline; oxo; pyrimido; acceptable salt; pharmaceutically acceptable
Prior art date: 1979-12-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000365968A

Other languages

English (en)

Inventor

Ikuo Ueda

Masanobu Nagano

Masayuki Kato

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Fujisawa Pharmaceutical Co Ltd

Original Assignee

Fujisawa Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-12-03

Filing date

1980-12-02

Publication date

1983-11-29

1980-12-02 Application filed by Fujisawa Pharmaceutical Co Ltd filed Critical Fujisawa Pharmaceutical Co Ltd

1983-07-12 Priority to CA000432297A priority Critical patent/CA1169062A/fr

1983-11-29 Application granted granted Critical

1983-11-29 Publication of CA1157858A publication Critical patent/CA1157858A/fr

Status Expired legal-status Critical Current

Links

125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 179
-1 nitro, amino Chemical group 0.000 claims abstract description 92
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 86
239000001257 hydrogen Substances 0.000 claims abstract description 83
150000002431 hydrogen Chemical class 0.000 claims abstract description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
XPBSKOLNCVNFGD-UHFFFAOYSA-N pyrimido[4,5-f]quinazoline Chemical class C1=NC=C2C=CC3=NC=NC=C3C2=N1 XPBSKOLNCVNFGD-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims description 100
239000000126 substance Substances 0.000 claims description 83
150000001875 compounds Chemical class 0.000 claims description 74
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
238000010438 heat treatment Methods 0.000 claims description 26
239000000460 chlorine Substances 0.000 claims description 19
125000005236 alkanoylamino group Chemical group 0.000 claims description 18
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 8
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000007529 inorganic bases Chemical class 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000005336 allyloxy group Chemical group 0.000 claims description 3
XNGKTZACMRYQRH-UHFFFAOYSA-N 10-(3-cyclopentylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)O)=CN=C3C2=CC=1NC(=O)CCC1CCCC1 XNGKTZACMRYQRH-UHFFFAOYSA-N 0.000 claims description 2
CXWIOSKVCSFMPR-UHFFFAOYSA-N 4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC=CC=C2N=CN2C1=NC=C(C(=O)O)C2=O CXWIOSKVCSFMPR-UHFFFAOYSA-N 0.000 claims description 2
SENAXMAZHLDISU-UHFFFAOYSA-N ethyl 10-(2-methylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O SENAXMAZHLDISU-UHFFFAOYSA-N 0.000 claims description 2
UUQFLDGNEYIIMP-UHFFFAOYSA-N ethyl 10-acetamido-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(C)=O)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O UUQFLDGNEYIIMP-UHFFFAOYSA-N 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 38
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 12
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 9
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 8
GLHFYRZBOMMQLW-UHFFFAOYSA-N 10-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC(NC(=O)C(C)(C)C)=CC=C2N=CN2C1=NC=C(C(O)=O)C2=O GLHFYRZBOMMQLW-UHFFFAOYSA-N 0.000 claims 7
YWYURKUOLLVUCU-UHFFFAOYSA-N 10-(2,3-dimethylpentanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC(NC(=O)C(C)C(C)CC)=CC=C2N=CN2C1=NC=C(C(O)=O)C2=O YWYURKUOLLVUCU-UHFFFAOYSA-N 0.000 claims 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
JBFFYVFSXPVAKA-UHFFFAOYSA-M sodium;10-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical group [Na+].C12=CC(NC(=O)C(C)(C)C)=CC=C2N=CN2C1=NC=C(C([O-])=O)C2=O JBFFYVFSXPVAKA-UHFFFAOYSA-M 0.000 claims 4
GVQQYCJUZDYHLN-UHFFFAOYSA-M sodium;10-(2,3-dimethylpentanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical group [Na+].C12=CC(NC(=O)C(C)C(C)CC)=CC=C2N=CN2C1=NC=C(C([O-])=O)C2=O GVQQYCJUZDYHLN-UHFFFAOYSA-M 0.000 claims 4
YNZXCFJFCCCJNC-UHFFFAOYSA-M 10-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate;tris(hydroxymethyl)-methylazanium Chemical compound OC[N+](C)(CO)CO.C12=CC(NC(=O)C(C)(C)C)=CC=C2N=CN2C1=NC=C(C([O-])=O)C2=O YNZXCFJFCCCJNC-UHFFFAOYSA-M 0.000 claims 3
CJUFCSAJFSXNNT-UHFFFAOYSA-M 10-(2,3-dimethylpentanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate;tris(hydroxymethyl)-methylazanium Chemical compound OC[N+](C)(CO)CO.C12=CC(NC(=O)C(C)C(C)CC)=CC=C2N=CN2C1=NC=C(C([O-])=O)C2=O CJUFCSAJFSXNNT-UHFFFAOYSA-M 0.000 claims 3
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
230000003301 hydrolyzing effect Effects 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
PMTRIOWLNORYCO-UHFFFAOYSA-N 10-(2-ethylbutanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC(NC(=O)C(CC)CC)=CC=C2N=CN2C1=NC=C(C(O)=O)C2=O PMTRIOWLNORYCO-UHFFFAOYSA-N 0.000 claims 1
GYASRBVTJZNZHA-UHFFFAOYSA-N 10-(3,3-dimethylbutanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC(NC(=O)CC(C)(C)C)=CC=C2N=CN2C1=NC=C(C(O)=O)C2=O GYASRBVTJZNZHA-UHFFFAOYSA-N 0.000 claims 1
LRXIXWFAPMLQLK-UHFFFAOYSA-N 10-(methanesulfonamido)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2N=CN2C1=NC=C(C(O)=O)C2=O LRXIXWFAPMLQLK-UHFFFAOYSA-N 0.000 claims 1
VZTHOHUVCBDVBO-UHFFFAOYSA-N 9-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylic acid Chemical compound C=1C(NC(=O)C(C)(C)C)=CC=C2C=1N=CN1C2=NC=C(C(O)=O)C1=O VZTHOHUVCBDVBO-UHFFFAOYSA-N 0.000 claims 1
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
AUONNNCQWMLBCZ-UHFFFAOYSA-N diethyl 6,18-dioxo-1,3,7,15-tetrazatetracyclo[12.4.0.02,7.08,13]octadeca-2,4,8,10,12,14,16-heptaene-5,17-dicarboxylate Chemical compound N12C(=O)C(C(=O)OCC)=CN=C2C2=CC=CC=C2N2C1=NC=C(C(=O)OCC)C2=O AUONNNCQWMLBCZ-UHFFFAOYSA-N 0.000 claims 1
OLXISSVKNKXQDX-UHFFFAOYSA-N ethyl 10-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(C)(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O OLXISSVKNKXQDX-UHFFFAOYSA-N 0.000 claims 1
FUPYREZOEIXKPV-UHFFFAOYSA-N ethyl 10-(2-ethylbutanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(CC)CC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O FUPYREZOEIXKPV-UHFFFAOYSA-N 0.000 claims 1
HDQJWXZBOLCUOI-UHFFFAOYSA-N ethyl 10-(3-cyclopentylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1NC(=O)CCC1CCCC1 HDQJWXZBOLCUOI-UHFFFAOYSA-N 0.000 claims 1
YAWUDBZUUGVKNS-UHFFFAOYSA-N ethyl 10-(4-methylpiperazin-1-yl)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1N1CCN(C)CC1 YAWUDBZUUGVKNS-UHFFFAOYSA-N 0.000 claims 1
RWJMTUUMGTUFNE-UHFFFAOYSA-N ethyl 10-(butanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)CCC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O RWJMTUUMGTUFNE-UHFFFAOYSA-N 0.000 claims 1
CWTXIBGKXMENRA-UHFFFAOYSA-N ethyl 10-(cyclohexanecarbonylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1NC(=O)C1CCCCC1 CWTXIBGKXMENRA-UHFFFAOYSA-N 0.000 claims 1
VZDAORQDNKMDFA-UHFFFAOYSA-N ethyl 10-(dimethylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(N(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O VZDAORQDNKMDFA-UHFFFAOYSA-N 0.000 claims 1
HIAUPFXRRDEQON-UHFFFAOYSA-N ethyl 10-(hexanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)CCCCC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O HIAUPFXRRDEQON-UHFFFAOYSA-N 0.000 claims 1
IGAINIGRAJGSTA-UHFFFAOYSA-N ethyl 10-(methanesulfonamido)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O IGAINIGRAJGSTA-UHFFFAOYSA-N 0.000 claims 1
SNHIYKGPFXTSKB-UHFFFAOYSA-N ethyl 10-benzamido-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1NC(=O)C1=CC=CC=C1 SNHIYKGPFXTSKB-UHFFFAOYSA-N 0.000 claims 1
NHYFCWPMNNPITD-UHFFFAOYSA-N ethyl 10-butyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(CCCC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O NHYFCWPMNNPITD-UHFFFAOYSA-N 0.000 claims 1
BIMKUKQLAZGJDO-UHFFFAOYSA-N ethyl 10-chloro-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(Cl)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O BIMKUKQLAZGJDO-UHFFFAOYSA-N 0.000 claims 1
VWIKKADTXJFFDV-UHFFFAOYSA-N ethyl 10-ethyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(CC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O VWIKKADTXJFFDV-UHFFFAOYSA-N 0.000 claims 1
UFIJVBJSEMYSNY-UHFFFAOYSA-N ethyl 10-ethylsulfanyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(SCC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O UFIJVBJSEMYSNY-UHFFFAOYSA-N 0.000 claims 1
ODORKCLEFWYKCD-UHFFFAOYSA-N ethyl 10-methyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(C)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O ODORKCLEFWYKCD-UHFFFAOYSA-N 0.000 claims 1
VFOKPFCXRXFFHN-UHFFFAOYSA-N ethyl 10-nitro-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O VFOKPFCXRXFFHN-UHFFFAOYSA-N 0.000 claims 1
PXQIDUGULOMHER-UHFFFAOYSA-N ethyl 4,6-dioxo-7h-pyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=CC=C2N=C(O)N2C1=NC=C(C(=O)OCC)C2=O PXQIDUGULOMHER-UHFFFAOYSA-N 0.000 claims 1
YZWSJUNZNOLXKB-UHFFFAOYSA-N ethyl 4-oxo-10-(propanoylamino)pyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)CC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O YZWSJUNZNOLXKB-UHFFFAOYSA-N 0.000 claims 1
BZIFQLHPNZZOQA-UHFFFAOYSA-N ethyl 4-oxo-10-[(2-phenylacetyl)amino]pyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1NC(=O)CC1=CC=CC=C1 BZIFQLHPNZZOQA-UHFFFAOYSA-N 0.000 claims 1
VXDJPARFFRPICV-UHFFFAOYSA-N ethyl 4-oxo-10-phenoxypyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OCC)=CN=C3C2=CC=1OC1=CC=CC=C1 VXDJPARFFRPICV-UHFFFAOYSA-N 0.000 claims 1
YPRHPFIYGJTOPV-UHFFFAOYSA-N ethyl 6-methoxy-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=CC=C2N=C(OC)N2C1=NC=C(C(=O)OCC)C2=O YPRHPFIYGJTOPV-UHFFFAOYSA-N 0.000 claims 1
HBZYYKAMXHKSLY-UHFFFAOYSA-N ethyl 6-methyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=CC=C2N=C(C)N2C1=NC=C(C(=O)OCC)C2=O HBZYYKAMXHKSLY-UHFFFAOYSA-N 0.000 claims 1
ASKZZFLORWVADR-UHFFFAOYSA-N ethyl 8-methyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=CC(C)=C2N=CN2C1=NC=C(C(=O)OCC)C2=O ASKZZFLORWVADR-UHFFFAOYSA-N 0.000 claims 1
YDNUCCULSGBIAP-UHFFFAOYSA-N ethyl 9,10-dimethoxy-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N=CN2C1=NC=C(C(=O)OCC)C2=O YDNUCCULSGBIAP-UHFFFAOYSA-N 0.000 claims 1
CPTOOYIBXGLKAQ-UHFFFAOYSA-N ethyl 9-acetamido-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=C(NC(C)=O)C=C2N=CN2C1=NC=C(C(=O)OCC)C2=O CPTOOYIBXGLKAQ-UHFFFAOYSA-N 0.000 claims 1
HRAVEPWQKRXYCP-UHFFFAOYSA-N ethyl 9-chloro-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=C(Cl)C=C2N=CN2C1=NC=C(C(=O)OCC)C2=O HRAVEPWQKRXYCP-UHFFFAOYSA-N 0.000 claims 1
YHQNYFISFPLLMZ-UHFFFAOYSA-N ethyl 9-methoxy-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=C(OC)C=C2N=CN2C1=NC=C(C(=O)OCC)C2=O YHQNYFISFPLLMZ-UHFFFAOYSA-N 0.000 claims 1
WIXNQCXQTRBGDK-UHFFFAOYSA-N ethyl 9-methyl-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=C(C)C=C2N=CN2C1=NC=C(C(=O)OCC)C2=O WIXNQCXQTRBGDK-UHFFFAOYSA-N 0.000 claims 1
YEDSXSULLCBUSB-UHFFFAOYSA-N methyl 10-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(C)(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O YEDSXSULLCBUSB-UHFFFAOYSA-N 0.000 claims 1
ZWNWZGRTNTWOQC-UHFFFAOYSA-N methyl 10-(2,3-dimethylpentanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(C)C(C)CC)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O ZWNWZGRTNTWOQC-UHFFFAOYSA-N 0.000 claims 1
QDUQASJKRDCRNL-UHFFFAOYSA-N methyl 10-(2-ethylbutanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(CC)CC)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O QDUQASJKRDCRNL-UHFFFAOYSA-N 0.000 claims 1
OPLWRHWJCHGTGR-UHFFFAOYSA-N methyl 10-(2-methylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)C(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O OPLWRHWJCHGTGR-UHFFFAOYSA-N 0.000 claims 1
SRZSPKWHYKSPRV-UHFFFAOYSA-N methyl 10-(3,3-dimethylbutanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NC(=O)CC(C)(C)C)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O SRZSPKWHYKSPRV-UHFFFAOYSA-N 0.000 claims 1
SKDVLOXRSAAMCN-UHFFFAOYSA-N methyl 10-(3-cyclopentylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OC)=CN=C3C2=CC=1NC(=O)CCC1CCCC1 SKDVLOXRSAAMCN-UHFFFAOYSA-N 0.000 claims 1
YFRXIJHOLYFALY-UHFFFAOYSA-N methyl 10-(cyclohexanecarbonylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C=1C=C2N=CN3C(=O)C(C(=O)OC)=CN=C3C2=CC=1NC(=O)C1CCCCC1 YFRXIJHOLYFALY-UHFFFAOYSA-N 0.000 claims 1
DTBVJGPDAINMGI-UHFFFAOYSA-N methyl 4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O DTBVJGPDAINMGI-UHFFFAOYSA-N 0.000 claims 1
CIEAZPWSWABNNA-UHFFFAOYSA-N methyl 9-(2,2-dimethylpropanoylamino)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC=C(NC(=O)C(C)(C)C)C=C2N=CN2C1=NC=C(C(=O)OC)C2=O CIEAZPWSWABNNA-UHFFFAOYSA-N 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical group OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 15
125000000217 alkyl group Chemical group 0.000 abstract description 12
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract description 12
125000004663 dialkyl amino group Chemical group 0.000 abstract description 8
125000003302 alkenyloxy group Chemical group 0.000 abstract description 7
125000004414 alkyl thio group Chemical group 0.000 abstract description 5
125000004442 acylamino group Chemical group 0.000 abstract description 4
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000004104 aryloxy group Chemical group 0.000 abstract description 3
208000006673 asthma Diseases 0.000 abstract description 3
230000000172 allergic effect Effects 0.000 abstract description 2
208000010668 atopic eczema Diseases 0.000 abstract description 2
208000024891 symptom Diseases 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 233
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 198
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 174
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CTNFEBGCGZNVDD-UHFFFAOYSA-N dimethyl 2-[[[6-(2-methylpropanoylamino)quinazolin-4-yl]amino]methylidene]propanedioate Chemical compound C1=C(NC(=O)C(C)C)C=C2C(NC=C(C(=O)OC)C(=O)OC)=NC=NC2=C1 CTNFEBGCGZNVDD-UHFFFAOYSA-N 0.000 description 1
MWCWDMOPXJSPMR-UHFFFAOYSA-N dimethyl 2-[[[6-(methanesulfonamido)quinazolin-4-yl]amino]methylidene]propanedioate Chemical compound C1=C(NS(C)(=O)=O)C=C2C(NC=C(C(=O)OC)C(=O)OC)=NC=NC2=C1 MWCWDMOPXJSPMR-UHFFFAOYSA-N 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
CJYQQUPRURWLOW-YDLUHMIOSA-M dmsc Chemical compound [Na+].OP(=O)=O.OP(=O)=O.OP(=O)=O.[O-]P(=O)=O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O CJYQQUPRURWLOW-YDLUHMIOSA-M 0.000 description 1
230000000694 effects Effects 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
NWEFSIMTOUJPRF-UHFFFAOYSA-N ethyl 4-oxo-10-propylpyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(CCC)=CC=C2N=CN2C1=NC=C(C(=O)OCC)C2=O NWEFSIMTOUJPRF-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000001341 hydroxy propyl starch Substances 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
235000013828 hydroxypropyl starch Nutrition 0.000 description 1
230000003053 immunization Effects 0.000 description 1
238000002649 immunization Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
229940090044 injection Drugs 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
MTJSABQOPBMXDF-UHFFFAOYSA-N methyl 10-(methanesulfonamido)-4-oxopyrimido[1,2-c]quinazoline-3-carboxylate Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N=CN2C1=NC=C(C(=O)OC)C2=O MTJSABQOPBMXDF-UHFFFAOYSA-N 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
VEGCMSDXDWEDSJ-UHFFFAOYSA-N n-(4-aminoquinazolin-6-yl)-2-methylpropanamide Chemical compound N1=CN=C(N)C2=CC(NC(=O)C(C)C)=CC=C21 VEGCMSDXDWEDSJ-UHFFFAOYSA-N 0.000 description 1
AXRIVJITPXKDFR-UHFFFAOYSA-N n-(4-aminoquinazolin-6-yl)-3-cyclopentylpropanamide Chemical compound C1=C2C(N)=NC=NC2=CC=C1NC(=O)CCC1CCCC1 AXRIVJITPXKDFR-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
RNWDENXDCQXZLH-UHFFFAOYSA-N quinazoline-4,6-diamine Chemical compound N1=CN=C(N)C2=CC(N)=CC=C21 RNWDENXDCQXZLH-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229940001607 sodium bisulfite Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical compound [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 description 1
UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
UANXSGVNVXTETO-UHFFFAOYSA-N trifluoro(hydroperoxy)methane Chemical compound OOC(F)(F)F UANXSGVNVXTETO-UHFFFAOYSA-N 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA000365968A 1979-12-03 1980-12-02 Derives de quinazoline Expired CA1157858A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000432297A CA1169062A (fr)	1979-12-03	1983-07-12	Derives de quinazoline

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB7941607		1979-12-03
GB7941607		1979-12-03
GB8031965		1980-10-03
GB8031965		1980-10-03
US06/384,998 US4429126A (en)	1979-12-03	1982-06-04	Sodium salt of 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-c]quinozoline-3-carboxylic acid
US384,998		1995-02-07

Publications (1)

Publication Number	Publication Date
CA1157858A true CA1157858A (fr)	1983-11-29

Family

ID=27260818

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000365968A Expired CA1157858A (fr)	1979-12-03	1980-12-02	Derives de quinazoline

Country Status (2)

Country	Link
US (1)	US4429126A (fr)
CA (1)	CA1157858A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010501593A (ja) *	2006-08-24	2010-01-21	セレネックス，インコーポレイテッド	イソキノリン、キナゾリンおよびフタラジン誘導体
MA41140A (fr) *	2014-12-12	2017-10-17	Cancer Research Tech Ltd	Dérivés de 2,4-dioxo-quinazoline-6-sulfonamide en tant qu'inhibiteurs de la parg
MA41179A (fr)	2014-12-19	2017-10-24	Cancer Research Tech Ltd	Composés inhibiteurs de parg
AR128846A1 (es)	2022-03-23	2024-06-19	Ideaya Biosciences Inc	Compuestos de indazol sustituidos con piperazina como inhibidores de parg

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3594379A (en)	1968-09-16	1971-07-20	Sandoz Ag	2,3-dihydroimidazo(1,2-c)quinazolines
CA986932A (en)	1970-08-27	1976-04-06	Shigeho Inaba	Process for preparing quinazoline derivatives
US4167569A (en)	1976-12-09	1979-09-11	Imperial Chemical Industries Limited	Pyrimido[1,2-a ]benzimidazole derivatives
US4105766A (en)	1977-08-19	1978-08-08	Sterling Drug Inc.	4,5-Dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylic acid derivatives
US4192944A (en)	1978-04-03	1980-03-11	Bristol-Myers Company	Optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-4-yl)carboxamides and their use as antiallergy agents

1980
- 1980-12-02 CA CA000365968A patent/CA1157858A/fr not_active Expired
1982
- 1982-06-04 US US06/384,998 patent/US4429126A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4429126A (en)	1984-01-31

Legal Events

Date	Code	Title	Description
2000-11-29	MKEX	Expiry

Publication	Publication Date	Title
CA1285943C (fr)	1991-07-09	Agents antitumoraux
JP2966929B2 (ja)	1999-10-25	製薬上活性のあるベンゾキナゾリン化合物
CA2499330C (fr)	2009-04-28	Nouvelles quinazolinones spiro-condensees et utilisation associee en tant qu'inhibiteurs de phosphodiesterase
CA1307786C (fr)	1992-09-22	Derives quinazoline et preparations antihypertension contenant les memescomposes comme ingredients actifs
US4490374A (en)	1984-12-25	5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use
JPH0794447B2 (ja)	1995-10-11	キナゾリン誘導体
EP0628032A1 (fr)	1994-12-14	Agents antiangineux a base de quinazolinone
US4543356A (en)	1985-09-24	Quinazoline derivatives
Shi et al.	2005	An efficient synthesis of quinazoline derivatives with the aid of low‐valent titanium reagent
CA1157858A (fr)	1983-11-29	Derives de quinazoline
JP3119758B2 (ja)	2000-12-25	７−アザインドール誘導体及びこれを有効成分とする抗潰瘍薬
US3993650A (en)	1976-11-23	Pyrrolo [3,4-d] pyrimidines
US4556739A (en)	1985-12-03	3,4-Dialkoxy-2-alkylcarbonyl analino compounds
US4258187A (en)	1981-03-24	Process for preparing quinazolinone oxides
US5405851A (en)	1995-04-11	Pharmaceutical compounds
US4608375A (en)	1986-08-26	Quinazolinone derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same
US4333937A (en)	1982-06-08	2-(Piperazinyl)-4-pyrimioinamines
CA1169062A (fr)	1984-06-12	Derives de quinazoline
US4631283A (en)	1986-12-23	Ortho substituted dihydroxy-2(1H)quinazolinone-1-alkanoic acids
EP0143001B1 (fr)	1991-04-10	Dérivés de la pyrimidoisoquinoléine
Fathy et al.	1988	Activated nitriles in heterocyclic synthesis: a one-step synthesis of several new pyrimidine, pyridine, and pyrazole derivatives
PL172906B1 (pl)	1997-12-31	Sposób otrzymywania indobufenu w korzystnej farmaceutycznie postaci krystalicznej
KR880002627B1 (ko)	1988-12-07	4(3h)-퀴나졸리논의 제조방법
KR840001287B1 (ko)	1984-09-07	퀴나졸린 유도체의 제조방법
Harris et al.	1979	Synthetic Plant Growth Regulators. The Synthesis of Co-Carboxyphenyl Derivatives of Pyrimidine